Imidazole → Silane, (3-chloro-2,2-dimethylpropoxy)trimethyl-

HRID 36755Notes

Reaction equation

HRID 36755 reaction equation
[CH3:1][Si:2](Cl)([CH3:4])[CH3:3].N1C=CN=C1.[CH3:11][C:12]([CH3:17])([CH2:15][Cl:16])[CH2:13][OH:14]>C1CCCCC1>[CH3:1][Si:2]([CH3:4])([CH3:3])[O:14][CH2:13][C:12]([CH3:17])([CH3:11])[CH2:15][Cl:16]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 6397Chlorotrimethylsilane2×HCID 834071-Propanol, 3-chloro-2,2-dimethyl-2×

Product 1

HCID 3018961Silane, (3-chloro-2,2-dimethylpropoxy)trimethyl-

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

The initiator of structure (3), designated PFI10, was prepared using the procedures broadly described in WO 91 112277. The hydroxyl functionality in 2,2-dimethyl-3-chloropropanol was protected by reaction with trimethylsilyl chloride. A solution of trimethylsilyl chloride (27.16 g, 0.25 mol) in dry cyclohexane (150 g) was treated with 20.4 g of imidazole (0.30 mol) under an argon atmosphere. The resulting slurry was stirred vigorously at room temperature as 2,2-dimethyl-3-chloropropanol (30.93 g, 0.25 mol) was added slowly to the mixture. The rate of addition was controlled to keep the reaction temperature below 40° C. The resulting slurry was filtered affording a clear solution of the desired 1-trimethylsilyloxy-2,2-dimethyl-3-chloropropane. Analysis using a Gas Chromatography-Mass Spectroscopy (GC-MS) technique found essentially no side products. The trimethylsilyl protected adduct was obtained in quantitative yield. A repeat of this experiment gave similar results.

Workup

  1. customwas prepared
  2. additionwas added slowly to the mixture
  3. additionThe rate of addition
  4. customthe reaction temperature below 40° C
  5. filtrationThe resulting slurry was filtered

Sources & evidence

ORD record
ord-378c79ed182d440eb6f83b18e5e65233
Source dataset
uspto-grants-1995_05
Patent number
US05416168

Reaction notes

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